IL278644B1 - A process for the stereoselective preparation of chiral 2-[(hetero)arylalkylsulfanyl]pyrimidines and products obtainable therefrom - Google Patents
A process for the stereoselective preparation of chiral 2-[(hetero)arylalkylsulfanyl]pyrimidines and products obtainable therefromInfo
- Publication number
- IL278644B1 IL278644B1 IL278644A IL27864420A IL278644B1 IL 278644 B1 IL278644 B1 IL 278644B1 IL 278644 A IL278644 A IL 278644A IL 27864420 A IL27864420 A IL 27864420A IL 278644 B1 IL278644 B1 IL 278644B1
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- optionally substituted
- salt
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 43
- 238000002360 preparation method Methods 0.000 title claims 7
- 125000005842 heteroatom Chemical group 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 230000000707 stereoselective effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- ZMQSLMZOWVGBSM-GXTWGEPZSA-N (2r)-2-[[2-amino-5-[(1s)-1-phenylethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound C1([C@H](C)SC=2N=C(C=3SC(N)=NC=3N=2)N[C@@H](CO)CC(C)C)=CC=CC=C1 ZMQSLMZOWVGBSM-GXTWGEPZSA-N 0.000 claims 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 2
- UUMGLXJQDAODOY-QMMMGPOBSA-N 6-amino-2-[(1s)-1-phenylethyl]sulfanyl-1h-pyrimidin-4-one Chemical compound S([C@@H](C)C=1C=CC=CC=1)C1=NC(N)=CC(O)=N1 UUMGLXJQDAODOY-QMMMGPOBSA-N 0.000 claims 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- ZMQSLMZOWVGBSM-UHFFFAOYSA-N 2-[[2-amino-5-(1-phenylethylsulfanyl)-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol Chemical compound N=1C=2N=C(N)SC=2C(NC(CO)CC(C)C)=NC=1SC(C)C1=CC=CC=C1 ZMQSLMZOWVGBSM-UHFFFAOYSA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 1
- 239000013058 crude material Substances 0.000 claims 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims 1
- 229910052808 lithium carbonate Inorganic materials 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical group CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (31)
1.Claims 1. A process for the preparation of a compound of formula I,
2.(I) or a salt thereof, wherein R represents aryl or pyridyl optionally substituted with one or more groups selected from halo, -CN, -C(O)NRR, -S(O)2R; C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, wherein the latter three groups are optionally substituted by one or more F; R represents C1-6 alkyl optionally substituted by one or more F; R and R each independently represent H or C1-6 alkyl optionally substituted by one or more F; R represents C1-6 alkyl optionally substituted by one or more F; which process comprises the steps of: (i) forming a compound of formula II,
3.(II) wherein R and R are as defined for a compound of formula I and R represents C1-6 alkyl optionally substituted by one or more F, or phenyl optionally substituted by one or more groups selected from halo, methyl and -NO2; by reacting a compound of formula III
4.(III) wherein R and R are as defined for a compound of formula I or II; with a suitable sulfonating agent in the presence of a suitable base B and a suitable solvent S, and subsequently (ii) reacting the compound of formula II, with a compound of formula IV,
5.(IV) wherein M+ represents Li+, Na+, K+ or Cs+ wherein the compound of formula III is provided as a single enantiomer. 2. A process as claimed in Claim 1, wherein the compound of formula II is not isolated from the reaction mixture from step (i) before it is used in step (ii). 3. A process as claimed in Claim 1 or Claim 2, wherein S is a solvent in which the salt formed between B and the leaving group of the sulfonating agent is insoluble. 4. A process as claimed in any one of Claims 1 to 3, wherein step (ii) comprises bringing a solution of a compound of formula II in a suitable solvent S into association with a solution of a compound of formula IV in a suitable solvent S. 5. A process as claimed in any one of Claims 1 to 4, wherein the process further comprises the step of: (iii) preparing a compound of formula IV by reacting a compound of formula V
6.(V) with a suitable base B in the presence of a suitable solvent S. 6. A process as claimed in Claim 4, wherein the solution of a compound of formula IV is obtained from step (iii), optionally after one or more purification steps.
7. A process as claimed in any one of the preceding claims, wherein S is selected from the group consisting of diethyl ether, methyl tert-butyl ether, 1,2-dimethoxyethane, 1,4-dioxane, tetrahydrofuran and 2-methyltetrahydrofuran.
8. A process as claimed in Claim 7, wherein S is methyl tert-butyl ether.
9. A process as claimed in any one of Claims 1 to 8, wherein B is an organic amine base.
10. A process as claimed in Claim 9, wherein B is triethylamine.
11. A process as claimed in any one of Claims 4 to 10, wherein S is a polar aprotic solvent.
12. A process as claimed in Claim 11, wherein S is N,N-dimethylformamide.
13. A process as claimed in any one of Claims 1 to 12, wherein B is selected from the group consisting of lithium hydroxide, lithium carbonate, sodium hydroxide, sodium carbonate, potassium hydroxide, potassium carbonate, caesium hydroxide and caesium carbonate.
14. A process as claimed in Claim 13, wherein B is sodium hydroxide.
15. A process as claimed in any one of Claims 1 to 14, wherein R represents aryl or pyridyl optionally substituted with one or more groups selected from halo, -CN, -SO2Me, or -CONH2.
16. A process as claimed in Claim 15, wherein R represents phenyl.
17. A process as claimed in any one of Claims 1 to 16, wherein R represents C1-3 alkyl.
18. A process as claimed in any one of Claims 1 to 17, wherein R represents methyl.
19. A process as claimed in any one of Claims 1 to 18, wherein the process further comprises the step of: (ib) removal of the salt formed between B and the leaving group of the sulfonating agent from the solution of a compound of formula II in S obtained from step (i).
20. A process as claimed in any one of Claims 1 to 19, further comprising the step of: (iv) treating the crude material obtained from step (ii) with a suitable solvent Sto cause precipitation of the compound of formula I.
21. A process as claimed in Claim 20, wherein S is acetonitrile.
22. A process as claimed in any one of Claims 1 to 21, wherein the sulfonating agent is mesyl chloride or tosyl chloride.
23. A process as claimed in any one of the preceding claims, wherein the process is a process for the preparation of a compound of formula Ia, or a salt thereof, (Ia) wherein R represents aryl or pyridyl, optionally substituted with one or more groups selected from halo, -CN, -C(O)NRR, -S(O)2R; C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, wherein the latter three groups are optionally substituted by one or more F, and R represents C1-6 alkyl optionally substituted by one or more F.
24. A process as claimed in Claim 23, wherein the compound of formula Ia is 6-amino-2-{[(1S)-1-phenylethyl]sulfanyl}pyrimidin-4-ol, or a salt thereof.
25. A process as claimed in claim 23 or 24, wherein the compound of formula I or Ia has a chiral purity of greater than 96%, preferably greater than 99%.
26. The compound 6-amino-2-{[(1S)-1-phenylethyl]sulfanyl}pyrimidin-4-ol, or a salt thereof, wherein the compound has a chiral purity of greater than 99.1%.
27. A process for the preparation of a compound of formula VII, or a salt thereof, (VII) wherein R represents aryl or pyridyl, optionally substituted with one or more groups selected from halo, -CN, -C(O)NRR, -S(O)2R; C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, wherein the latter three groups are optionally substituted by one or more F, and R represents C1-6 alkyl optionally substituted by one or more F, wherein the process comprises a process as defined in any one of Claims 1 to 22.
28. A process as claimed in Claim 27, wherein the process is for the preparation of 2-[(2-amino-5-[(1-phenylethyl)thio][1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol, or a salt thereof, .
29. A process as claimed in Claim 28, wherein the process is a process for the preparation of (2R)-2-[(2-amino-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol, or a salt thereof. .
30. A process as claimed in Claim 29, wherein the (2R)-2-[(2-amino-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol has a chiral purity of greater than 99.2%.
31. A process for the preparation of a pharmaceutical formulation comprising a compound as defined in any one of Claims 1 to 25 or 27 to 30, or a compound as claimed in Claim 26, or a salt thereof, which process is characterised in that it includes a process as defined in any one of Claims 1 to 22.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1807898.0A GB201807898D0 (en) | 2018-05-15 | 2018-05-15 | New processes and products with increased chiral purity |
| PCT/EP2019/062530 WO2019219771A1 (en) | 2018-05-15 | 2019-05-15 | A process for the stereoselective preparation of chiral 2-[(hetero)arylalkylsulfanyl]pyrimidines and products obtainable therefrom |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| IL278644A IL278644A (en) | 2021-01-31 |
| IL278644B1 true IL278644B1 (en) | 2023-11-01 |
| IL278644B2 IL278644B2 (en) | 2024-03-01 |
Family
ID=62623275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL278644A IL278644B2 (en) | 2018-05-15 | 2019-05-15 | A process for the stereoselective preparation of chiral 2-[(hetero)arylalkylsulfanyl]pyrimidines and products obtainable therefrom |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US11542281B2 (en) |
| EP (1) | EP3793981A1 (en) |
| JP (1) | JP7225379B2 (en) |
| KR (1) | KR20210014646A (en) |
| CN (1) | CN112218853A (en) |
| AU (1) | AU2019270348B2 (en) |
| CA (1) | CA3099865A1 (en) |
| GB (1) | GB201807898D0 (en) |
| IL (1) | IL278644B2 (en) |
| MX (1) | MX2020012108A (en) |
| SG (1) | SG11202011317PA (en) |
| WO (1) | WO2019219771A1 (en) |
| ZA (1) | ZA202007101B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB202006849D0 (en) | 2020-05-08 | 2020-06-24 | Kancera Ab | New use |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006107258A1 (en) * | 2005-04-06 | 2006-10-12 | Astrazeneca Ab | Novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA56992C2 (en) * | 1995-05-08 | 2003-06-16 | Фармація Енд Апджон Компані | a- pyrimidine-thioalkyl substituted and a- pyrimidine-oxo-alkyl substituted compounds |
| SE9802729D0 (en) | 1998-08-13 | 1998-08-13 | Astra Pharma Prod | Novel Compounds |
| GB0217431D0 (en) | 2002-07-27 | 2002-09-04 | Astrazeneca Ab | Novel compounds |
| GB0221829D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
| GB0328243D0 (en) * | 2003-12-05 | 2004-01-07 | Astrazeneca Ab | Methods |
| WO2006008171A1 (en) * | 2004-07-22 | 2006-01-26 | Dsm Ip Assets B.V. | Process for the preparation of a diastereomerically enriched compound |
| HN2005000795A (en) * | 2004-10-15 | 2010-08-19 | Aventis Pharma Inc | PYRIMIDINS AS ANTAGONISTS OF PROSTAGLANDINA D2 RECEPTOR |
| JP2013010750A (en) | 2011-06-02 | 2013-01-17 | Taisho Pharmaceutical Co Ltd | Medicine containing two-pyridone compound |
| RU2617696C2 (en) * | 2012-02-17 | 2017-04-26 | ЭЙСАЙ Ар ЭНД Ди МЕНЕДЖМЕНТ КО., ЛТД | Methods and compounds that can be used to synthesize orexin-2 receptors antagonists |
| JP2015231988A (en) | 2014-05-12 | 2015-12-24 | 大正製薬株式会社 | 2- pyridone compound |
-
2018
- 2018-05-15 GB GBGB1807898.0A patent/GB201807898D0/en not_active Ceased
-
2019
- 2019-05-15 JP JP2021514480A patent/JP7225379B2/en active Active
- 2019-05-15 WO PCT/EP2019/062530 patent/WO2019219771A1/en unknown
- 2019-05-15 IL IL278644A patent/IL278644B2/en unknown
- 2019-05-15 SG SG11202011317PA patent/SG11202011317PA/en unknown
- 2019-05-15 CA CA3099865A patent/CA3099865A1/en active Pending
- 2019-05-15 KR KR1020207035250A patent/KR20210014646A/en unknown
- 2019-05-15 MX MX2020012108A patent/MX2020012108A/en unknown
- 2019-05-15 US US17/055,172 patent/US11542281B2/en active Active
- 2019-05-15 CN CN201980032185.5A patent/CN112218853A/en active Pending
- 2019-05-15 EP EP19726334.6A patent/EP3793981A1/en active Pending
- 2019-05-15 AU AU2019270348A patent/AU2019270348B2/en active Active
-
2020
- 2020-11-13 ZA ZA2020/07101A patent/ZA202007101B/en unknown
-
2022
- 2022-10-14 US US17/966,294 patent/US11691988B2/en active Active
-
2023
- 2023-05-19 US US18/199,899 patent/US20230322807A1/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006107258A1 (en) * | 2005-04-06 | 2006-10-12 | Astrazeneca Ab | Novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives |
Non-Patent Citations (1)
| Title |
|---|
| SOFIA KARLSTR?M ET AL,, SUBSTITUTED 7-AMINO-5-THIO-THIAZOLO[4,5- D ]PYRIMIDINES AS POTENT AND SELECTIVE ANTAGONISTS OF THE FRACTALKINE RECEPTOR (CX 3 CR1), 25 April 2013 (2013-04-25) * |
Also Published As
| Publication number | Publication date |
|---|---|
| IL278644A (en) | 2021-01-31 |
| US20230068240A1 (en) | 2023-03-02 |
| CN112218853A (en) | 2021-01-12 |
| US11542281B2 (en) | 2023-01-03 |
| ZA202007101B (en) | 2023-05-31 |
| US20210188873A1 (en) | 2021-06-24 |
| MX2020012108A (en) | 2021-02-18 |
| KR20210014646A (en) | 2021-02-09 |
| JP7225379B2 (en) | 2023-02-20 |
| GB201807898D0 (en) | 2018-06-27 |
| EP3793981A1 (en) | 2021-03-24 |
| WO2019219771A1 (en) | 2019-11-21 |
| US11691988B2 (en) | 2023-07-04 |
| US20230322807A1 (en) | 2023-10-12 |
| JP2021523950A (en) | 2021-09-09 |
| AU2019270348B2 (en) | 2024-01-18 |
| SG11202011317PA (en) | 2020-12-30 |
| CA3099865A1 (en) | 2019-11-21 |
| AU2019270348A1 (en) | 2020-12-03 |
| IL278644B2 (en) | 2024-03-01 |
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